Acid-catalyzed depolymerization of coal by hydride donors. Quarterly report, November 1, 1983-January 31, 1984. [Naphthalenethiol; di-l-naphthyl sulfide]

Technical Report · Sun Jan 01 00:00:00 EST 1984

OSTI ID:5371532

Miller, B

The rate of reductive desulfuration of 1-naphthalenethiol by potassium iodide and trifluoromethane sulfonic acid in trichloroacetic acid increased with the addition of small amounts of water. Quantitative yields of naphthalene were obtained from 1-naphthalenethiol at 140/sup 0/C in trichloroacetic acid solutions containing from 2 to 8 wgt. % of water. The product was stable indefinitely under these reaction conditions. In contrast, the yield of naphthalene obtained using anhydrous conditions reached a maximum of ca. 60% and then decreased at longer reaction times, presumably due to the occurrence of electrophilic substitution and other side reactions. Similarly, reductive desulfuration of di-1-naphthyl sulfide in anhydrous trichloroacetic acid gave a maximum of ca. 1.5 moles of naphthalene per mole of sulfide, after which the yield of naphthalene began to decrease. In contrast, addition of ca. 4 wgt. % of water resulted in more rapid desulfuration and the formation of essentially quantitative yields of naphthalene.

• Research Organization: Massachusetts Univ., Amherst (USA). Dept. of Chemistry
• DOE Contract Number: FG22-82PC50805
• OSTI ID: 5371532
• Report Number(s): DOE/PC/50805-T2; ON: DE84007328
• Country of Publication: United States
• Language: English

Related Subjects

01 COAL, LIGNITE, AND PEAT
37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
COAL
DEPOLYMERIZATION
CONDENSED AROMATICS
REDUCTION
HYDRIODIC ACID
CHEMICAL REACTIONS
NAPHTHALENE
CHEMICAL REACTION YIELD
ORGANIC SULFUR COMPOUNDS
DESULFURIZATION
THIOLS
ACETIC ACID
CATALYTIC EFFECTS
CHEMICAL REACTION KINETICS
EXPERIMENTAL DATA
HIGH TEMPERATURE
ORGANIC CHLORINE COMPOUNDS
POTASSIUM IODIDES
RESEARCH PROGRAMS
STRUCTURAL MODELS
SULFONIC ACIDS
WATER
ALKALI METAL COMPOUNDS
AROMATICS
CARBONACEOUS MATERIALS
CARBOXYLIC ACIDS
DATA
DECOMPOSITION
ENERGY SOURCES
FOSSIL FUELS
FUELS
HALIDES
HALOGEN COMPOUNDS
HYDROCARBONS
HYDROGEN COMPOUNDS
INFORMATION
INORGANIC ACIDS
INORGANIC PHOSPHORS
IODIDES
IODINE COMPOUNDS
KINETICS
MATERIALS
MONOCARBOXYLIC ACIDS
NUMERICAL DATA
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXYGEN COMPOUNDS
PHOSPHORS
POTASSIUM COMPOUNDS
REACTION KINETICS
YIELDS
010405* - Coal
Lignite
& Peat- Hydrogenation & Liquefaction
400301 - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)